EP2164941B1 - Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence - Google Patents

Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence Download PDF

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Publication number
EP2164941B1
EP2164941B1 EP08751003.8A EP08751003A EP2164941B1 EP 2164941 B1 EP2164941 B1 EP 2164941B1 EP 08751003 A EP08751003 A EP 08751003A EP 2164941 B1 EP2164941 B1 EP 2164941B1
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EP
European Patent Office
Prior art keywords
preferentially
active ingredient
water
solid particles
hydrophobic group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP08751003.8A
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German (de)
English (en)
French (fr)
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EP2164941A1 (fr
Inventor
Olivier Guerret
Jean-Marc Suau
Yves Kensicher
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Coatex SAS
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Coatex SAS
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the invention relates to a new method for formulating odorous active principles so as to protect them during an application on the skin or on another support such as a textile (in the case of a laundry for example) or a wall (in the case of a painting for example), and so as to control the progressive release of said active ingredients after their application. It relies on the use of acrylic and water-soluble emulsions with a pH greater than 5, containing hydrophobic groups. These emulsions make it possible to encapsulate odorant active principles in order to promote their protection vis-à-vis the environment while slowing down their kinetics of release, which will result in an increase in the duration of the effectiveness of the perfume (phenomenon of remanence).
  • Odorant Active Ingredient in the context of this invention, we mean by this expression any substance having an olfactory detectable activity. For a better understanding, it will be possible to use in the Application the shortened expression of "active ingredient”, in order to designate the "odorant active principle”.
  • Perfume this term refers in this application to any formulation containing at least one odorant active ingredient.
  • HASE Anglo-Saxon acronym for Hydrophobically Alkali Swellable Emulsion. This term refers to acrylic thickeners based on (meth) acrylic acid, an ester of these acids and a hydrophobic monomer.
  • the modes of administration of the perfumes are varied: however, improve their behavior at the level of the initial perfume formulation as well as at the level of the surface on which they are applied is an important constraint for the skilled person. Indeed, the odorant active ingredients contained in the perfume formulations may be chemically unstable and vulnerable to external aggressions (such as oxidation).
  • the first category uses ⁇ -cyclodextrins, which are natural "host” molecules obtained by enzymatic degradation of the starch. They are in the form of cyclic oligomers of glucose and are characterized by the presence of a cavity that allows them "to host a host molecule", so as to form a complex of inclusion: according to this mechanism, they can encapsulate odorant active principles, as described in particular in the document EP 0 392 606 . However, complexes based on ⁇ -cyclodextrins and an active ingredient must undergo an additional coating step from a protective material (waxes or fatty alcohols), so as to form a wall that will allow the gradual release of active ingredient. In addition, the stability of the inclusion complex formed depends primarily on the affinity of the cyclodextrin with the principle to be encapsulated: many active ingredients can not be encapsulated by ⁇ -cyclodextrins.
  • a second method consists in encapsulating an odorant active ingredient by means of silicone emulsions in water, as described in the document US 5,130,171 .
  • the high permeability of silicones to gases allows them to slowly release the molecules of active principles.
  • such a method relies on the solubility or the compatibility of the active ingredient to be encapsulated with the silicone emulsion used, which does not therefore make it possible to encapsulate all the odorant active principles.
  • the coacervation processes require the prior realization of an emulsion of the active ingredients to be encapsulated, which constitutes a step in addition to that of coacervation.
  • this technique does not allow the encapsulation of water-soluble active ingredients, since it can not be carried out in emulsion.
  • this method relies on the compatibility of the active ingredients with the polymers used for coacervation.
  • polycondensation Another encapsulation method based on the use of polymers is polycondensation. This method relies on the polycondensation of 2 monomers, one being compatible with the encapsulation medium, the other being compatible with the substance to be encapsulated.
  • the document WO 2007/004166 it describes polyurethane capsules containing an active ingredient, said capsules being obtained by reaction between a polyisocyanate compound and a guanidine salt with diols. This process is, however, limited to the active ingredients which do not react chemically with the isocyanates: it is therefore not possible to encapsulate alcohols, amines or acids.
  • Another method of encapsulation based on polymers is the method of forming a film in the presence of surfactants. This method is based on the choice of a polymer compatible with the active ingredient to be encapsulated. An emulsion of said polymer is prepared in aqueous medium in the presence of the active ingredient to be encapsulated and of surfactants.
  • the document US 4,803,195 describes the use of cellulosic polymers or polyvinyl alcohol, while the document WO 2005/032503 refers to acrylic polymers.
  • JP-2005298474 discloses a content composition of the perfume.
  • EP 1 655 351 A2 discloses aqueous formulations containing HASE type polymers.
  • HASE type emulsions which have an associative hydrophobic monomer.
  • This monomer has the property, when the emulsion is neutralized to a sufficiently high pH (> 5), to create associative interactions which reinforce the thickening effect compared to a polymer which does not have such monomers.
  • These associative interactions between the hydrophobic groups delimit domains which are as many solvation cages for an active ingredient.
  • One of the merits of the Applicant is to have been able to identify and use the structuring phenomenon of water via a HASE type emulsion, at pH greater than 5: thus naturally protecting the active principles dissolved in this solution.
  • step a) of the process according to the invention a mixture is obtained in which the molecules of active principle are trapped in solvation cages. Even after application and drying of the resulting formulation on a support (skin, fabric, wall, etc.), the active ingredients remain trapped within the polymer film that has formed during drying: the speed of Evaporation of the active ingredient by diffusion through the film.
  • This decrease in pH causes the collapse of the polymer structure: a dispersion in water of solid particles consisting of the polymer and the active ingredients is then obtained.
  • the active ingredients remain trapped: they remain protected and their rate of evaporation is reduced.
  • step b) it is possible to implement both step b) but also a subsequent step c), which consists in isolating the solid particles obtained after step b), by removing the water.
  • step c consists in isolating the solid particles obtained after step b), by removing the water.
  • the active ingredients are isolated and thus protected while evaporating more slowly.
  • Another advantage of the invention is that it can be used to trap a very large number of odorous active ingredients. Indeed, the skilled person has access to a very broad library of associative monomers in which he can draw to identify the monomer that will have the best possible affinity for the active ingredient to trap.
  • step a) implements step b).
  • the method according to the invention implements step a) then step b) then step c).
  • the process according to the invention is also characterized in that the pH of the mixture, during step a), is adjusted by means of an organic or inorganic base.
  • the constituents active principle, water, HASE type emulsion, as well as the mineral or organic base
  • the order of introduction will be chosen by those skilled in the art, especially as a function of the solubility in water of the active ingredient to be encapsulated.
  • the process according to the invention is also characterized in that, in step a), 0.1% to 20%, preferably 0.1% to 10%, and most preferably 0.1% are used. % to 5% by dry weight of a HASE emulsion, relative to the total weight of the aqueous formulation obtained after step a).
  • the process according to the invention is also characterized in that, in step a), from 0.1% to 20% by dry weight of an odorant active ingredient which is hydrophilic or hydrophobic, compared with to the total weight of the aqueous formulation obtained after step a).
  • the process according to the invention is also characterized in that a medium or strong acid is used during step b).
  • the HASE emulsion contains at least one copolymer of (meth) acrylic acid, of a non-water-soluble monomer which is preferably a (meth) acrylic ester chosen very preferably among ethyl acrylate, butyl acrylate, methyl methacrylate and mixtures thereof, and a monomer containing at least one hydrophobic group.
  • the method according to the invention is finally characterized in that the water is removed by evaporation or centrifugation during step c).
  • the person skilled in the art implement any other technique for removing water from the mixture obtained after step b).
  • Another object of the invention is the formulation consisting of solid particles dispersed in water, and obtained by carrying out the precipitation step b) of the previously described method.
  • This dispersion of solid particles in water is characterized in that the solid particles which constitute it contain at least one odorant active ingredient and at least one copolymer of (meth) acrylic acid, of a non-water-soluble monomer which is preferentially a (meth) acrylic ester chosen very preferably from ethyl acrylate, butyl acrylate, methyl methacrylate and mixtures thereof, and from a monomer containing at least one hydrophobic group.
  • Another object of the invention resides in the formulation consisting of the solid particles obtained by carrying out the isolation step c) of the process previously described.
  • These solid particles are characterized in that they contain at least one odorant active ingredient and at least one copolymer of (meth) acrylic acid, of a non-water-soluble monomer which is preferably a (meth) acrylic ester chosen very preferably from ethyl acrylate, butyl acrylate, methyl methacrylate and mixtures thereof, and a monomer containing at least one hydrophobic group.
  • a non-water-soluble monomer which is preferably a (meth) acrylic ester chosen very preferably from ethyl acrylate, butyl acrylate, methyl methacrylate and mixtures thereof, and a monomer containing at least one hydrophobic group.
  • a final subject of the invention is the use of aqueous formulations of at least one odorant active ingredient, aqueous dispersions of solid particles of at least one odorant active ingredient and solid particles of at least one odorant active ingredient, as agent having the dual function of protecting an odorant active ingredient and to slow down its evaporation.
  • This example illustrates the process of the invention, in which, according to step a), an aqueous formulation of an odorant active ingredient and a HASE emulsion at a pH greater than 5 are produced.
  • step b) of the process of the invention which consists in reducing the pH to a value of less than 5.
  • step c) of the invention which leads to isolate the solid particles of encapsulated active ingredient.
  • This example thus also illustrates the 3 embodiments of the formulation according to the invention: a solution obtained after step a), a dispersion of solid particles in water obtained after step b), and solid particles and dried after step c).
  • Each dispersion resulting from tests no. 1b to 5b is placed in an oven at a temperature of 110 ° C. for a time such that 99.5% by weight of the initial water is evaporated.
  • Solid particles are then obtained which contain the odorant active ingredients tested, and which are verified to not leak any detectable odor at the level of smell.
  • This example illustrates the process of the invention, in which, according to step a), an aqueous formulation of an odorant active ingredient and a HASE emulsion at a pH greater than 5 are produced.
  • step b) of the process of the invention which consists in reducing the pH to a value of less than 5.
  • This example thus also illustrates the two embodiments of the formulation according to the invention: a solution obtained after step a), a dispersion of solid particles in the water obtained after step b).
  • This example illustrates the process of the invention, in which, according to step a), an aqueous formulation of an odorant active ingredient and a HASE emulsion at a pH greater than 5 are produced.
  • step b) of the process of the invention which consists in reducing the pH to a value of less than 5.
  • step c) of the invention which leads to isolate the solid particles of encapsulated active ingredient.
  • This example thus also illustrates the 3 embodiments of the formulation according to the invention: a solution obtained after step a), a dispersion of solid particles in water obtained after step b), and solid particles and dried after step c).
  • test No. 9 which is a control
  • the mass of water used is 100 grams.
  • the active ingredient tested is aurantiol.
  • test 9a which illustrates the invention, the same mass of active principle is introduced into water as for test No. 9.
  • a quantity of polymer which is an emulsion of the type is introduced.
  • the aurantiol is in the form of droplets not missible with water.
  • a gel is observed: the odorant active ingredient molecules are solvated by the polymer and are dispersed in the continuous phase.
  • the pH of the solution corresponding to test No. 9 bis is lowered to a value equal to 2.45, by addition of phosphoric acid.
  • Their diameter is equal to about 1900 nm.
  • the dispersion is placed in a vacuum oven at a temperature of 45 ° C for a time such that 99.5% by weight of the initial water is evaporated.
  • Solid particles are then obtained which contain the odorant active ingredients tested.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Medicinal Preparation (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP08751003.8A 2007-06-01 2008-05-20 Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence Active EP2164941B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0703890A FR2916655B1 (fr) 2007-06-01 2007-06-01 Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence
PCT/IB2008/001275 WO2008146119A1 (fr) 2007-06-01 2008-05-20 Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence

Publications (2)

Publication Number Publication Date
EP2164941A1 EP2164941A1 (fr) 2010-03-24
EP2164941B1 true EP2164941B1 (fr) 2016-03-30

Family

ID=38959609

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08751003.8A Active EP2164941B1 (fr) 2007-06-01 2008-05-20 Procede pour formuler des principes actifs odorants afin de les proteger et d'augmenter leur remanence

Country Status (11)

Country Link
US (1) US8461098B2 (ja)
EP (1) EP2164941B1 (ja)
JP (1) JP2010529225A (ja)
KR (1) KR20100025550A (ja)
CN (1) CN101679914A (ja)
DK (1) DK2164941T3 (ja)
ES (1) ES2579442T3 (ja)
FR (1) FR2916655B1 (ja)
IL (1) IL201797A (ja)
PL (1) PL2164941T3 (ja)
WO (1) WO2008146119A1 (ja)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2918540B1 (fr) * 2007-07-12 2011-01-14 Coatex Sas Procede de formulation de principes actifs agrochimiques pour reguler leur cinetique de liberation, les proteger des agressions exterieures et securiser leurs utilisateurs
FR3000084B1 (fr) * 2012-12-20 2015-02-27 Coatex Sas Microparticules d'agent actif
FR3012814B1 (fr) * 2013-11-06 2018-01-26 Arkema France Composition polymere comprenant et liberant un compose actif odorant
CN103865649B (zh) * 2014-03-04 2015-11-04 北京英茂药业有限公司 一种用于干花的加香剂及其制备方法
FR3032629B1 (fr) 2015-02-18 2017-02-17 Coatex Sas Microparticules polymeriques
FR3032972B1 (fr) * 2015-02-20 2019-05-10 Arkema France Polymeric composition absorbing, comprising and releasing an odoriferous active compound, method for preparing it and its use

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FR2792545B1 (fr) * 1999-04-20 2001-06-01 Oreal Composition foisonnee, son procede de fabrication et son utilisation notamment comme composition cosmetique
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AU2003200070B2 (en) 2002-01-25 2008-01-24 Rohm And Haas Company Triggered response compositions
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FR2839658B1 (fr) * 2002-05-17 2004-08-06 Protex Nouveau procede de preparation de microcapsules a base de gelatine, contenant un liquide hydrophobe et microcapsules obtenues
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Also Published As

Publication number Publication date
JP2010529225A (ja) 2010-08-26
ES2579442T3 (es) 2016-08-11
IL201797A0 (en) 2010-06-16
EP2164941A1 (fr) 2010-03-24
US20100152094A1 (en) 2010-06-17
FR2916655A1 (fr) 2008-12-05
KR20100025550A (ko) 2010-03-09
US8461098B2 (en) 2013-06-11
WO2008146119A1 (fr) 2008-12-04
CN101679914A (zh) 2010-03-24
DK2164941T3 (en) 2016-06-06
IL201797A (en) 2013-12-31
FR2916655B1 (fr) 2009-07-24
PL2164941T3 (pl) 2016-09-30

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